Ryan Phillippe

Biography

She's the Boss

While jointly presenting the award for Best Makeup at the 2001 Academy Awards with Witherspoon, Phillippe makes a joke about his wife's earning power. "Let me read it?" she asks him. "You make more than I do," he quips, pointing at the envelope. "Go ahead."

2003

October 23

Growing Pains?

Phillippe and Witherspoon add a son, Deacon, to the family. They take turns filming so one parent is always at home with the children. Both acknowledge the difficulties in being a young star couple. They talk openly about being in couples therapy and constantly working on their relationship. "We're normal people with normal problems," Witherspoon says to PEOPLE. Phillippe concurs, telling NewYorkDailyNews, "The biggest mistake is...having the marriage fall apart because of laziness."

2006

January 16

Celebrate Gold Times

When Witherspoon wins a Golden Globe for her portrayal of June Carter in Walk the Line, Phillippe celebrates, waving his arms in the air, screaming and jumping. In October, he explains his behavior to Rolling Stone, "I was plastered [at the Golden Globes]! Shirley MacLaine and I drank like crazy, just putting away bottles of wine and making fun of everyone." In the same interview, he also describes his desire to live in the Caribbean, "probably smoking herb."

March 05

More Than a Pretty Face

The actor plays an impressionable rookie, opposite Matt Dillon's racist cop, in Crash. The movie wins Best Picture the night Witherspoon takes home the Oscar for Best Actress. Phillippe tells the LosAngelesTimes, "She's great at what she does. I am proud of her."

October 27

Soldier On

Phillippe turns in another critically acclaimed performance, this time as a leading man, in Clint Eastwood's war drama, Flags of Our Fathers. He plays one of the flag-raising heroes featured in the historic Iwo Jima photograph. Rolling Stone applauds his portrayal of John "Doc" Bradley, the film's "emotional center," as a "hauntingly implosive performance." Phillippe tells the ChicagoSun-Times, "This is the first film where I had this immediate feeling that my children will be proud of their father."

Phillippe in Stop-Loss

Phillippe stars in Stop-Loss, with Cornish and Channing Tatum. In the film, which is written and directed by Kimberly Peirce (BoysDon'tCry), Phillippe plays a soldier who returns home and refuses to go straight back to Iraq.

June

Ryan Moves On

With ex-wife Witherspoon with Jake Gyllenhaal, Phillippe moves on with his love life as well, stepping out with Cornish at the 2008 Australian in Film Breakthrough Awards. "They were adorable," says a guest of the couple, who have been under the watchful eye of the media for months. In February 2010, the couple calls it quits.

2010

May 21

Comedic Relief

Fresh from his rocky breakup with Cornish, Phillippe brings the laughs in MacGruber, a big-screen adaptation of the popular Saturday Night Live sketches starring Will Forte and Kristen Wiig. "It was just something I never thought people would let me do," the actor says of turning to comedy. "Making MacGruber, I had a hard time not breaking with Will. I would dig my fingernail into my thumb."